


Belle of the Ball

by Castello (orphan_account)



Category: The Office (US)
Genre: Bottom!Dwight, Crossdressing, Enemies to Friends, Enemies to Lovers, First Time, Grinding, Humor, Jim is secretly a poet, LARPing, M/M, Misunderstandings, Porn With Plot, Seduction, Sensuality, Someone actually shows Dwight affection, top!jim
Language: English
Status: Completed
Published: 2020-01-17
Updated: 2020-01-17
Packaged: 2021-02-27 15:15:34
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,898
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22289263
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/Castello
Summary: It takes Jim a minute to kick his brain back into gear again and start processing.It's got to be the wig, Jim thinks, because there's no other reason for Dwight's face to look ages softer than it does in the office.And the dress...Or... Jim gets stuck babysitting his nephew at a LARPing convention. Apparently Dwight LARPs in dresses. Things get out of hand.
Relationships: Jim Halpert & Dwight Schrute, Jim Halpert/Dwight Schrute
Comments: 16
Kudos: 174





	Belle of the Ball

Jim would give almost anything to be back at the office at this particular moment. Or just to be _anywhere_ other than here.

Beside him, Jim's nephew, Andy, is clipping cheap metal over a shirt of (equally cheap quality) chainmail. Jim watches in disgruntled fascination. The outfit itself is pretty terrible; looks akin to something just shy of a halloween store and uncomfortable in addition, but the outfit certainly looks realistic enough in terms of set up. Andy clasps a set of metal bracelets around his wrists before moving on to the boots. They look even less comfortable. Jim'll give him props for his dedication at least.

"There's a tunic and a cape in the backseat for you." Andy says tersely, buckling a sword to his waist to finish off the ensamble.

Jim snorts, "Nah, I think I'm good. But thanks."

Andy looks up at him with a frown, "You have to. They're not going to let you in if you're wearing day clothes. Medieval wear only. Just put it on."

Jim shoves his hands into his pockets before nodding towards Andy's get-up, "I don't have pants or fancy boots."

"Mom got those for you. She said she put them in your trunk yesterday."

Of course. One of the benefits (or in this case downsides) of being a twin is that they know things about you normal siblings wouldn't, and they enjoy using that knowledge to torment you at least 10% more than regular siblings.

"I'm not taking my pants off out here in the open."

"You were _supposed_ to change into those _before_ we got here." Andy replies testily, annoyed with Jim, like this is somehow _his_ fault.

Babysitting his teenage nephew at a LARPing convention wasn't exactly how Jim had planned to spend his weekend either.

Sure, maybe there's some joy to be taken from watching all these sad thirty year olds dress up for what Jim would consider 'the theatrical version of dungeons and dragons'... but there's only so much fun Jim can get from pranking these guys, and even less so without someone else there to be in on the joke with him.

Jim sighs, "Where can I change?"

Andy's head drops back with a frustrated noise. He makes this almost... gurgle in the back of his throat. "Ugh, okay fine. You can change after we get in. There's a bathroom in the tavern."

Jim grins, "You mean the park lodge?"

Andy glares at him.

Holding up his hands in surrender, Jim walks over to open the trunk and pulls out the bag his sister has so graciously left for him. He'll get her back for it later. For now, he's got tights, a tunic, and knee high boots to struggle into.

His nephew finishes suiting up, clicks a sword belt around his waist, then leads them over to the front. General entry gets paid. They check in with only a little bit of grumbling from the guy that takes their money, _insisting_ that Jim be wearing something other than "clothes from the future", but it gets sorted. Andy speaks up for him, tells the guy that Jim is new and that he'll be changing as soon as they get into the tavern. The guy grumbles, but lets them through. 

_Goody._

God forbid Jim be forced to go home because he’d shown up in cashmere instead of chainmail. 

Jim's only a little weirded out by the oddly large amount of people past the entrance. He'd have thought more people would be shy about this kind of thing but these guys seem really in their element. They're having fun even, all out in the open. Jim kind of appreciates it.

"How many people do you think are here?" He asks Andy offhandedly as they trudge towards the 'tavern'.

"There's usually hundreds! And Tammy said they get more crowded every year."

Jim quirks an eyebrow, "Who's Tammy?"

"My friend." he answers quickly, _too_ quickly in fact, and Jim smirks as he carries on, "She works here. She's a dwarven-blacksmith. We're gonna be hanging out after I figure out how to ditch you."

Jim snorts, "Just like that? Announce it without any trickery? Didn't your mother teach you any better?"

Andy grins, pointing to the lodge that's had a large, crudely carved, wooden sign placed over the original one for the lodge, "We both know you'd see through me anyway. I'm gonna ditch you either way... so it would just be easier on both of us if I get it out in the open now and we both go on with our days. You can pretend you were a good babysitter when my mom asks, and I'll pretend you haven't been putting clothespins on everybody since we got out of the car."

Jim smirks proudly and lets Andy lead him into the tavern to point out the bathroom. He gives Jim a quick list of very specific do's and don'ts, they shake hands to seal their mutual understanding, and then say their goodbyes.

Well.

He's got a few hours to kill. Jim kind of wants to look around, but the people sitting in the lodge are all giving him dirty looks (no doubt for his 'future clothes’) so he decides to change first. Jim weaves his way through tables and chairs and into the bathrooms, relieved to find it's still a modern day stall and not... a _pot_ or something. He sighs through his bag, and starts to shed his socks and shoes.

In the end, the ensemble as a whole isn't so bad. Of course, Jim's not going to make a habit of wearing tunics and tanned-leather boots to work, but the red really brings out the color in his face and the brown of his curls. The boots are a slightly weird fit, but they're comfortable enough, coming up just below his knee. There's a belt that Jim remembers belongs on the _outside_ of his shirt, which is just stupid really, but it works. Jim's surprised by the cape though. It's dark, another shade of brown, with a hood in the back and a plastic clip in the front that's supposed to look copper.

When Jim's done he leaves the stall and takes a look at himself in the mirror above the sink.

It's weird, for sure... but not exactly unflattering. Jim wonders if Pam would think it amusing if he wore this into the office and whipped the hood over his head menacingly, pretending to be some shady... what are they called? Rogues? Of course, Dwight would probably tell him off for 'incorrectly representing a _real_ rogue', but it would only make it all the better. Much more amusing if Dwight reacts because he’s annoyed. 

Jim would never admit to it, but he secretly likes Dwight. He's fun to mess with, if nothing else. Teasing him helps make the work day go by a lot faster, and sometimes Jim just needs a way to let loose after being cooped up at a desk for eight hours _five days of the week._

He finally leaves the restroom, the bag (now holding his street clothes) tucked under his arm and hidden beneath his cloak. The hood rests idle on his back, a weird and foreign weight around his neck, but he's not bothered by it enough to flip it over his head. Jim finds a seat at a recently abandoned table in a corner towards the back, sets his bag down, and waits patiently to be served.

As he waits, Jim observes the rest of the room.

The place is fairly large, for a start, and even though Jim’s been to this place when it’s not tricked out in fake candles and huge barrels of what’s supposed to be mead(but it’s probably just root beer), it’s hard to imagine what it looked like previously.   
  
The hanging animal heads had always been there (Jim distinctly remembered the activist protest over them that kept him from going fishing that weekend) and the large wood tables and benches too, though admittedly there were originally fewer. Small wooden stools had been stuffed in around what used to be the check in desk, and shelving had been put in behind it to hold tin mugs and plates. Considering the menu only offered a few things (mainly drinks) Jim didn’t have to wonder why they hadn’t tried to get a building with a kitchen. 

People are crammed into the benches at long tables, some drinking and singing happily enough to make Jim wonder if maybe they _were_ serving alcohol from those colossal barrels.

As Jim finds settled into his seat in the back corner, he notices a couple of groups whistling and poking at one of the servers. He can’t see her face, but he has no trouble staring at the long blonde hair and velvety green dress that don’t exactly hide her—sorry— _his_ natural figure, but it somehow does, strangely, manage to make it femininely flattering. 

Jim smirks, crossing his arms over his table to watch as this no faced server pinches someone’s cheek and punches another in the arm before handing out drinks. 

Whoever he is, he’s clearly friendly with the group and more than comfortable confidently wandering around in a long, heavy looking dress, hip out to hold the tray as he pushes his long hair over a shoulder and continues to serve everyone cheerfully. 

Jim had to give him props, he’d never be able to pull off something like that. Especially not that _well_. 

Excited to meet this mystery server Jim lifts his arm to call out for a drink, dropping it like gravity has suddenly tripled when his mystery server finally turns and Jim gets a chance to look at his face. 

_A very familiar face._

Without thinking Jim whips the hood over his head and slumps a little in his seat, hoping not to be noticed before he can look again.

Maybe it was a trick of the light...

Jim peeks out from under the safety of his hood.

Nope. It’s definitely him. 

A laugh from his familiar, crossdressing barmaid confirms it. 

Somehow, the man _not_ tripping over a floor length, velvety dress as he gracefully weaves through the tables is the one and only, insufferable, Dwight Schrute.

It takes Jim a minute to kick his brain back into gear again and start processing.

It's got to be the wig, Jim thinks, because there's no other reason for Dwight's face to look ages softer than it does in the office. The serpent-green colored contacts draw more attention to his face overall, and without the glasses, they're much easier to see. Jim's distracted by the fake ears poking through the long strands of equally fake, perfectly straight, blonde hair, but not enough to miss the way the entire ensemble is pulled together by Dwight's smile.

Because he's _smiling openly_.

To _people_.

Dwight _never_ smiles.

He's got some sort of complex about it actually. Jim explicitly remembers Dwight claiming it as a sign of submission in primates, he'd even mocked him for it quite a few times later. Dwight's almost _never_ smiled in front of anyone at the office before, let alone Jim. But here he is, grinning wide and bright at strangers that order drinks and make some scandalous, teasing comments about his attire. Jim feels a little twist in his gut over it; probably because he's just so damn confused by this new side of Dwight that he's never seen before.

Crossdressing.

Who knew, right?

Jim pulls the hem of his hood to better cover his face when Dwight turns more in his direction to collect two empty mugs off an abandoned table. There are some coins scattered beside them, and dwight sweeps them with uncharacteristic gracefulness into the pocket of his apron. Jim wonders if he's actually getting paid for this in real, usable, American dollars, or if he's just in here dressed like a barmaid for kicks. Not that he would be. Jim just can't imagine Dwight being the kind of guy to get off on dressing like a girl, let alone a girl who _serves_. At the very least, that's not the kind of image Dwight usually projects. He's always putting off lame 'macho' vibes that really just make him seem more pathetic.

But maybe that's intentional.

He's _here_ in any case, isn’t he? 

And he's in a goddamn _dress_.

Jim watches quietly for another few minutes, jaw hanging ever so slightly open when Dwight saunters—yes, he fucking _saunters_ —Jim’s way, before he's finally recognized. Dwight's only a couple of steps away from waiting on his table when he stops dead in his tracks and Jim knows without a doubt he's been caught.

Dwight's eyes widen, those falsely green gazers shrinking away with surprise, and his mouth tips open in a way that has absolutely no right to look as inviting as it does. After getting a look at a bit of the color inside of his mouth, Jim can now see that he's wearing some light lipstick too. He takes another look, wondering if Dwight's actually wearing a full face of makeup and he just didn't notice. Maybe that would explain how he looks so... Jim doesn’t even know the word.

When Dwight blinks incredulously, Jim can practically picture him putting on the mascara that makes his eyelashes look so much longer than normal.

Dwight is still quiet, just staring at Jim, so Jim takes the initiative, raises his hand to give a light little wave, and grins, "Hey Dwight." he bites back the urge to grow his smile, "Nice dress."

It's like snapping his fingers, the effect is so jarring.

Dwight's eyes wet and glisten, and maybe it's still the entire get-up that's got Jim knocked so far off his horse, but his heart gives a little lurch. Dwight immediately purses his lips, drops his tray on the table, hikes up his skirts in a wish of motion and turns. Jim is still a little dazed by the time Dwight has made a run for the door.

Some of the other patrons call out to him with disappointment, but Jim's too busy jumping up from his seat to pay them much mind.

He has to backtrack for a second, almost forgetting the little bag of his day clothes before Jim tails after him.

Jim follows Dwight out of the tavern and into the street. Yelling voices echo from tents that have been set up along a dirt path and immediately distract. There are people _everywhere_ , and it gets hard to keep up with Dwight pretty quick. There are elves popping up left and right; people with long, blonde, flowy wigs, and dresses that distract his attention away from finding the runaway elf he's actually looking for. If Jim had seen all of these other guys first he might have thought Dwight's outfit was actually a little plain by comparison, but that plainness works to Dwights advantage. He blends into the crowd too well and Jim loses him.

Ordinary as his clothes may have been in comparison, the shock of _Dwight_ being in them is still fresh, and Jim's attention doesn't stay on anyone else for very long.

He blames that goddamn dress.

Jim officially runs out of leads in between the blacksmith's tent and the stage where a Jester is putting on a juggling show. He grumbles, running a hand down his face with a grimace, and makes a short walk of defeat towards the blacksmith tent.

Jim's relieved to see a familiar face when he arms open the tent flap, even if he’s only given a bratty death glare in return for his arrival.

Andy is talking with a girl, pretty red hair curled just past her shoulders, cheeks covered in freckles, and a full set of armor similar to Andy's, but it looks like real metal. Jim might be impressed if it didn't seem like such a colossal waste of time and resources. God, he's being affected by the office. He needs to get out of the office more.

Andy isn't at all pleased to see him. He frowns at Jim, crossing his arms, "I thought we had a deal, dude."

"I saw someone I know." Jim says stupidly.

Andy uncrosses his arms and makes a place for Jim to sit, "Really? Who?"

"A guy from work." Jim says, then sets his bag down, "He was in a dress."

The redhead, Tammy, Jim presumes, shrugs, "A handful of people crossdress here, but it could also have been an elven gown-"

"I mean... he had pointy ears and... like, a blonde wig, but... that definitely looked like a dress. The guys in the lodg- in the _tavern_ ," he corrects when Andy stares him down, "were catcalling him."

Tammy cocks her head, "Oh! Are you talking about Dwight?"

Jim's head lifts, "You know him?"

"Oh sure! He and Mose are regulars here. They usually work in the tavern, and Dwight actually looks kinda pretty as a girl, so he always gets whistled at." she snorts, "Hard to forget those guys, they always bring pounds and pounds of beets to contribute to the market. They tried to make that their entry payment one year, you know."

Jim nods, "Yep. That's the one. I work with him."

Tammy quirks her lips, "So what happened? Did you guys talk? Why are you here?"

Andy grunts, "Yeah. Why _are_ you here?"

Tammy elbows him in the arm, but the plastic armor takes a lot of the blow for him.

"He, uh..." Jim bumbles, "I actually think I startled him. Do you-" he frowns, "Do you know where he might be if he's not in the tavern?"

Shrugging Tammy says, "You could try his tent? Those boys usually set up on the edge of the campground. Brown tent with big wood stakes sticking out towards the forest." she explains, "Says that's the best way to deter bear attacks in the night, but I think he just likes having stakes around his tent."

Jim nods again, smiling, "Yeah, that's definitely my guy."

Tammy grins, "Your boyfriend?"

"What?" Andy says at the same time Jim squawks out, "Excuse me?"

"You’ve got to be the mystery boyfriend, right? Mose says he's always going on about his boyfriend from work."

"What!" Andy repeats, louder, more incredulous, and with 60% more smile, "Oh, wait 'till mom hears about this!"

"Dwight doesn't have a boyfriend." Jim says firmly, or at least tries to, "and even if he did, it certainly isn't me."

Tammy's eyes look him up and down, "Well, I’ve always wondered if he made him up to keep ha day customers away, but you certainly look like a 'stupidly handsome idiot' to me."

Jim frowns and tosses his bag at Andy's face to stop him from laughing. "I've gotta go-"

"Yeah, yeah." Tammy smiles, "Tell him I said hi, and the beet bread this year was pretty good."

Jim can't resist it, " _Beet_ bread?" he snorts.

She grins back, "Long story."

"Okay." Andy says insistently, shooing Jim out, "I'll hold onto your clothes, so get going. Go find your boyfriend. Shoo."

"He's not my-"

"Yeah, yeah, go already."

Jim stops complaining when he sees the slight blush on his nephew's cheeks. He grins. Definitely a schoolboy crush then, like he'd suspected. He waves to Tammy and pinches Andy's cheek just to get back at him, simpering when he squeaks, bats Jim's hand away and yells at Tammy to stop laughing.

Jim thinks they’re kinda cute together.

He gets lost a few times trying to find the campground, but eventually comes across a pole of little arrow signs that prove less helpful than he’d have liked, but helpful enough. Jim's thankful they hadn't come up with some otherworldly name to cover up 'campground'. It would have made his job a lot harder.

Jim makes a beeline for the perimeter, remembering what Tammy had said about the ‘bear spikes’ and starts following it, on the lookout for a brown tent with a crossdressing paper salesman.

Leave it to Dwight to always be the most entertaining—if not annoying—person in the room. 

The hunt takes him all the way to the farthest corner of the camp before he finally spies a brown tent, the back surrounded with large wooden stakes, and even a wooden crate of beets resting outside the front. It’s almost like a big neon sign reading “DWIGHT IS HERE”.   
  
He stops just short of the entrance, wondering what the heck he’s supposed to say when he goes in. Apologize? He didn’t really do anything except say hello. He could ask Dwight why he ran, but Jim already knows it’s probably because he was afraid Jim would tease him. Which, sure, okay, he definitely might have, but not now. Not if it was a real insecurity. This was obviously a secret for Dwight, a safe space he could be free to do this, and Jim had trudged into his sacred place and trampled it. 

He sighs, rubbing the back of his neck awkwardly before steeling his composure. He flips up the tent flap, head held high, and wanders in. 

Only to catch a pillow to the face. 

Jim walks in to find Dwight sitting at what seems to be a makeshift vanity; two crates set up on their sides, a long wood plank serving as the table top, with a mid-sized mirror, some cosmetic oddities, and a creepy, blank mannequin head. 

Probably for the wig...

Dwight turns with a startled yelp, very quickly grabbing up the pillow from the cot set up beside him and throwing it at Jim’s head. 

”God, get out of here!” he shouts, “How did you find me? Get out!” 

Jim braces himself as Dwight stands and the blanket gets thrown too, Jim only managing to catch it sloppily just before it can sweep the carpet laid out under them.

”Dwight, calm down.” He tries, failing for better words. 

”No!” Dwight shouts, a little louder, “You’re here to make fun of me! I don’t know how you found out, but if you say a _word_ I’ll-!” 

Jim turns his shoulder forward just in time to keep the book from hitting his chin. 

“Dwight-!” He tries again, coming forward a few steps to try and stop him from wrecking the whole tent. 

What if he decided to throw a box next?

”Shut up and get out! Just leave me alone!” 

Jim tosses his blanket back onto the bed and in the process catches a punch in the same shoulder that had been hit by the book. 

“Ow!” He gripes, turning back to catch Dwight by his wrists before he can hit him again, “Dwight! Take a breath!”

Dwight fights him angrily, brokenly, using the last of his strength to jostle Jim a bit before he finally, reluctantly, gives up. Slumping and still in Jim’s hold, Dwight deflates, sinking down until he’s sitting on the cot, head hanging low enough that the wig covers his face.

“Are you going to stop throwing things now if I let you go?” 

“No.” He says, childishly.

Jim waits. 

“ _Fine_. I won’t hit you. Just leave me alone.”

”I wanna talk, Dwight.” 

Dwight scoffs, “You mean _make fun of me_.” 

“No.” Jim says honestly, sort of surprising himself.

He really didn’t want to make fun of Dwight. It hadn’t been a thought on his mind. He— well, Jim didn’t know exactly what _did_ want to do, but it wasn’t to make of of him.

”I’m not gonna make fun of you.” 

Dwight sniffs and Jim wonders if he’s crying. He crouches down low, low enough to see the skin under Dwight’s eyes has gotten just a little puffy and red, but there aren’t tears yet. 

He looks almost soft, vulnerable, and it’s all so jarring that the only thing Jim can dumbly think to say is, “I’m sorry, Dwight.” 

Dwight sucks in a shaky breath, finally looking Jim in the eye. “What?” 

“I’m sorry. I didn’t mean to make you cry.” 

Dwight clamps off again, turning his face away and trying to struggle out of Jim’s hold on his wrists. Jim pushes them against Dwights thighs instead, leaning forward into the hold and effectively trapping Dwights’s arms at his sides. 

During the process he gets a feel of the dress fabric against his hands; velvety, like it looked, and warm from Dwights body heat. Dwight makes a pathetic little sound that’s so uncharacteristic—

Jim’s heart rate picks up a beat.

”I’m not gonna make fun of you.” He says again.

Dwight scoffs a little louder, “Yeah, right. I bet you think this is really funny. You caught me. I’ll never be able to show my face again. Hah hah.” 

Jim frowns because there _is_ a tear now. It’s just one shimmering streak down a cheek, but it’s still a tear. 

A tear from _Dwight_. 

Jim is still just kind of bewildered by this whole situation. He can’t imagine the same uptight stick in the mud he works with being open and vulnerable enough to do something like wear a dress in public. It seems so contrary to his character at the office, he’d taken Jim completely by surprise. He doesn’t want to mock it, Jim wants to applaud it.

It feels like Dwight has been working on a secret cocoon behind Jim’s back, and while he’d been a fool, distracted by Dwight’s charactoral misdirection, the ugly caterpillar he thought he knew well had been secretly living a double life as a butterfly. 

Jim wants to keep this a secret too. Selfishly. _His_ secret. He wants to privately observe this kind of beauty—bravery really. 

It’s very brave. 

Dwight shedding down to a layer of openness enough to publicly crossdress—and hell, to be _good_ at it, is braver than anything Jim is capable of. As open and carefree as he likes to seem, Jim doesn’t let himself be vulnerable with people often, if ever. If the fiasco of emotional wreckage with Pam wasn’t enough to prove that, years of grudges against his boss, discontent for his co-workers, and plenty of other examples sure could. 

Jim doesn’t like feeling vulnerable. Doesn’t like sharing how he really feels. Doesn’t like being upfront and honest about what he wants or likes. It leaves him too open to get hurt or disappointed. 

But this...

Jim likes this side of Dwight best because he _wants_ it. Can’t have it, doesn’t even have the balls to try. 

It’s so _brave_... 

“I like it.” He says dumbly, a horrible verbal sum up of his whole inner dialogue. 

Dwights gaze almost snaps to him, it’s so sudden, “You _what_?” 

And Jim’s not imagining the way Dwights breathing has gotten just a little faster. Where he’s holding Dwights wrists he can feel the quickening pulse. 

“I like it...” he repeats, distracted and still utterly stupefied by this whole thing. 

Dwight takes in a quick drag of air, eyes wide and chest visibly heaving. He wets his lips.

Oh. 

God, Jim hadn’t meant it like that at all, but he sort of wants to when he sees Dwight lick his lips, the lipstick fading a little near the inside with the sultry swipe of his tongue. 

Jim can’t help it, “Lipstick?” 

Dwight blinks, eyes finally moving away from what Jim realizes was _his own_ mouth. _Shit_. 

Jim’s arousal stirs. 

“It... it completes the look. My lips are too dark to be elvish... so... the pale pink...”

It’s absurd, but Jim’s broken brain registers that as dedication instead of the mock-worthy dorkiness it should be. He lets out a small hum, low, and revels in the way Dwights eyes seem to glaze a little as he hears it. They're not serpent green anymore, he notices finally, and decides in an endeavor to kill two birds with one stone, leaning forward until he can rest his head against Dwight’s—are they really trembling?—thighs. He looks up, seeing his whole face a little better. 

“Colored contacts?” 

Dwight gives him a small nod, “To go with the dress.” He says, like that’s such an obvious line of thinking, and Jim smiles _with teeth._  
  
“Get more noticed that way, so I get more tips...” 

Jim hums again, deciding to add a nod, face still pressed against Dwight’s lap, each shift if his head swishing the skirt fabric up just a tantalizing half inch. 

“And you like getting noticed?” 

Dwight makes another noise, and from where he’s resting Jim realizes he’s at a perfect level to see exactly how much Dwight likes _Jim_ noticing, at least. 

_Shit. Shit. Shit._

Dwight shakes his head, “The money-“ 

“That’s not what I asked.” Jim says, and turns his head one more time so that when he speaks, the heat of his breath will hopefully ghost over the hopeful stirrings of Dwight’s erection. 

It probably doesn’t make it through the fabric, but Dwight seems well affected anyway. 

“..I do...” he says, bashfully, in a near whisper, cheeks even pinker than before. “And... people like the dress...” 

Jim squeezes one wrist in a form of silent instruction for Dwight’s hand to stay where it is as he speaks, carefully drawing it away when he thinks Dwight’s got the message.

”And the dress,” he half-groans, enjoying another little twitch in the steadily growing buldge beside his face. Jim’s free hand slowly slides down a leg, following the skirt hem until he reaches the bottom, where he carefully slips cold fingers underneath and over Dwight’s ankle, “Do you like the dress too?” 

Dwight gasps and Jim knows he has him. He shifts from a crouch to a knee, pushing himself up just enough to get his mouth nearer, dragging his hand up Dwight’s leg and revealing a scandalous bit of skin in the process. 

Dwight _whimpers_. Fucking _whimpers_ , and Jim’s lost. Dwight’s finally gotten the best of him. After always trying to poke holes in Jim’s composure, this is it. This was all it took. Fucking _c_ _rossdressing_. Jim feels like a wreck, and he’d give Dwight the fucking moon right now if he asked for it. Anything he wants. 

Jim finally releases Dwight’s other hand and pushes himself up off the ground enough to creep into Dwight’s personal space. His mouth lingers by Dwight’s neck as hands come up to his shoulders. They don’t push him away though, they just... sort of _cling_. 

Jim can hear his own heartbeat in his ears, body begging to close that little bit of space and make a damn move. Do something about the arousal they’re both clearly feeling over this. 

Jim takes the leap. 

He bites. 

A delicious little half-moan tumbles out of Dwight’s mouth before he can catch it, and Dwight bites his own lip afterword to quiet himself, which of course Jim just can’t have. He’s got to see all the ways Dwight’s been holding out on him all this time. That includes what his moans sound like.

Dwight’s been doing this for some time now, how many years has he been secretly squeezing into dresses and putting on lipstick? How many people have gotten to see this before Jim had? 

Jim dares to be bolder, one palm pressing against Dwight’s chest until he’s horizontal on the bed, one of Jim’s knees tucked in between his legs, the other hand rucking up the dress enough to let Jim in without getting the tail end caught between them. 

“I like it.” Jim mumbles against the skin just under Dwight’s jaw, “I like it a lot.” 

Dwight fists his hands in the front of Jim’s tunic, muttering in a way that shows he’s as wrecked as Jim is, “I can’t- you don’t- I don’t understand-”

”What?” Jim asks, and leans back enough to look down where he’s been groping Dwight’s legs, continually amazed, “And you shaved?” His smirk turns filthily devious when he looks back up at Dwight’s face, “You can’t even pretend that was for someone else to see.”

Dwight groans as Jim starts in on the other side of the neck, hand trailed up and up, Dwight’s trembling leg following and bending near Jim’s hip. 

It puts Dwight’s crotch in a position to ride Jim’s knee, and when he starts helplessly grinding away, Jim just can’t find it in himself to stop him. 

His hand finally makes it up to Dwight’s underwear and Jim pauses, yet _another_ beautiful surprise. Dwight is the gift that just keeps on giving.

Dwight shakes under him, staring at Jim like he’s waiting for him to say something, anything, so Jim let’s his eyes close slowly, composure slipping away fast, “Dwight...” he says, careful, slower than a snail, “Are you wearing _panties_?” 

Dwight gulps, and looks so fucking sinfully pleased with himself. It’s a little more familiar that be manages to also be embarrassed at the same time. But there’s a little coyness there. More new things. Jim’s lost patience, he’s too excited. What will he uncover next?

This man, Dwight Schrute, is the world’s greatest con man, keeping everyone fooled into thinking he was just an annoying, wimpy workaholic who spent way too much time trying to be someone he wasn’t. Instead he drips honey, glitter, _gold_ , he’s a treasure trove of new excitement and his essence is fucking made up completely of sensualism and surprise. 

Maybe that’s too poetic for describing a dirty leg grind in a dress, but Jim’s obsessed. He’s going to learn how to write sonnets. 

“ _Shit!”_ Jim finally says aloud and stops supporting himself on one arm, electing instead to get two hands on Dwight’s legs, slotting himself in between and using his new leverage to pull Dwight close enough to be sitting on his thighs. 

Close enough to rut back against him in a frenzy, for the cot to shake and creak and for Dwight to slam a shaky hand over his own mouth to keep from screaming. Jim digs teeth in, rubs his little bit of stubble over Dwight’s clean shave, licks, _grinds_ , does everything he can until Dwight finally gasps, “Jim, stop or I’ll-!” And shakes violently with an orgasm. 

Jim forces himself to slow down, catch a breath, and promises himself the rewards of maybe getting more if he doesn’t push too hard just now. 

He kisses where he’s bitten, drinking in every lusty little whimper as Dwight whines his name out, “Jim, I’m sorry I-”

”Don’t be sorry.” He says encouragingly, and starts his way down the long line of Dwight’s dress, “You ever gone a couple rounds at one time before?” 

It’s really just offhanded conversation to distract himself, trying to tame down his own erection enough to carry on forward, but it _is_ a good thing to know. That and, “Ever had sex with a guy before?” 

Dwight pushes the wig away from his head, sweating and gasps, “I...” he breathes, “I’ve never really spent a lot of time... having sex before...” his lips smack when he takes a gulp, “Quick in, done and out... it’s most efficient.”

Jum huffs out a laugh, bitting a little through the dress where he figures Dwight’s hip bone would be, “Sex isn’t about _efficiency_ Dwight.” 

Dwight chuckles, and Jim’s heart _sings_ , “I’m starting to understand that...” 

Jim hums, “And?” 

Dwight’s quiet for another second, “Jerked off with a man once. He offered to use his mouth but I.. didn’t accept.” 

Shiiiit. Jim pauses, looking up from where he’s almost reached the end of the gown, _so close_ , “Is it something you want?” 

Dwight looks down at him, maybe a little dizzy with the post-orgasm high as he licks his lips and nods. 

It’s enough for Jim. He mumbles a small, “Okay” and “I’ll be gentle.” Before finally slithering down the final few inches.

As Jim parts the cloth of the dress, he ponders eating Dwight out. Jim fantasizes about getting lost in these frilly skirts, Dwight's trembling fingers trying to find his head in the mess of fabric while jim drives him out of his mind with his tongue. Jim's always had a quick mouth, and if previous reviews were anything to go by, it had definitely translated over into the bedroom _well_.

Dwight sighs shakily when Jim licks and nips at his inner thigh, and Jim feels the desire all over again.

"Can I eat you out?" he mumbles into the skin there, not willing to lift his head away long enough to properly ask.

”Wh-what?” 

Jim delivers another light bite and says again louder, “Can I eat you out?” 

Dwight makes a startlingly high-pitched sound, and though Jim can’t see it he can imagine the shy, stubborn, quick shake of his head as he says, "No."

Jim pouts, a little disappointed, but obeys. Maybe if he's lucky, Dwight will let him do it some other time. He'd better make sure he does a good enough job. At least good enough to leave Dwight wanting more.

His fingers curl around the lace and silk _(Jesus, Dwight)_ so that he can pull them down and away. He’s not at all surprised to find them just a little wet and sticky with cum when he gets them down to knee level. 

Some deeply caged, perverted part of himself wants to suckle on them, maybe so Dwight can see, see if Dwight finds it sexy that Jim’s made him cum in his panties too...

He brings his head out from under the skirts, removing the underwear and crawling up until he’s comfortably nestled between Dwight's legs, arms bracketing the man in a way that somehow makes him seem smaller than usual, “Can I fuck you?" He asks next.

Another startled sound, this time Dwight squeezes his eyes shut, gripping his skirts in tight fists, "...Y-Yes." he sighs, "But- but first can you..?"

"Yeah?"

Dwight blinks a few times, staring at where the collar of Jim’s tunic is loose enough to show off his collar bone, “Uhm... Could you kiss me first?”

Jim’s a little befuddled by that question originally, thinking it a pretty simple request with an even simpler answer, but Dwight's uncharacteristically shy demeanor says otherwise. 

Maybe kissing means a lot more to Dwight than it does to Jim. Maybe he doesn’t—he _probably_ doesn’t—get kissed that often, and there seems to be a special insecurity behind doing so in this outfit. 

”Yeah.” He says simply, lamely, without any sort of idea what he _should_ say to a question like that. Especially with how Dwight asks it.

Dwight is still giving off some weirdly shy energy that Jim doesn’t know what to do with as he brings his hands up between them to barely touch Jim’s cheeks. It seems like he means to cup his face, but only his fingers really make contact. 

Jim stares as Dwight’s eyes flicker between looking at his mouth and his nose, like he’s not quite sure what to do with this unforeseen obstacle. Jim doesn’t smirk, trying not to make fun, but he is amused. Instead, he takes pity on him and leans in, tilting his head enough that they can kiss without awkwardly bumping noses. 

It’s not an especially epic kiss, but it’s nice. Dwight takes an extra second to shut his eyes into it and doesn’t really move his mouth, but that’s okay. Jim takes the lead and shifts a little, one palm cupping his cheek, turning him as he needs. He pulls back well before they can run out of air, but they still end up panting. 

“I thought you and Angela hooked up a lot?” Jim blurts before his brain realizes that’s a bad, very bad idea. 

Dwight blinks, but does respond, “Yes. But uh, it was different.” 

Jim can’t help it, “How? Didn’t you kiss?” 

Dwight frowns, “Well yes, but... it was different.” 

“ _How_?” 

Dwight goes pink, and now Jim does want to tease. 

“She was on her back. Now I’m on mine.” Dwight says, somewhat bitter maybe. He scoffs, “You talk more than I would have thought.” 

Jim grins, “Just wondering why you kiss like it’s your first time.” 

“Well it’s not.” He snaps, defensive, “Just different.” 

“Because I’m a guy?” 

“Because you’re... well, _you_.” He says. 

Jim feigns offense, but his hand starts wondering, ready to get back on the road. “Why am I different?” 

“ _You_ ,” Dwight starts, but seems unable to continue, “You... never mind.”

Dwight gasps when Jim gets a hold of Dwight’s soft prick, squeezing and stroking languidly.

“But I want to kno _w_.” The last word comes out a little like a a child complaining. 

Dwight bites a lip, “Weren’t you going to...” 

“Yeah.” Jim says, and already cogs are turning in his head of all the possible ways he’d like to have Dwight. 

He’ll wait for all that. He’ll tease and taunt, rile Dwight up until he’s _begging_ for Jim to do more. All the time. 

Instead he ducks his head under the dress, sucks Dwight’s hardening cock into his mouth and presses his thumb over his hole.

* * *

Later, when Jim reunites with Andy, he doesn’t bother to answer when he asks why Jim’s tunic belt has mysteriously disappeared, and in response, Jim doesn’t comment on the lipstick stain on Andy’s cheek. 

They climb into the car, Jim puts it into reverse and agrees way too quickly when Andy asks, “Wanna come back with me tomorrow?” 

_Hell yes_.


End file.
